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Theoretical study of azido gauche effect and its origin

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2017
3_2906_C7NJ00369B.pdf (2.198Mb)
Аутори
Baranac-Stojanović, Marija
Stojanović, Milovan
Aleksić, Jovana
Чланак у часопису (Рецензирана верзија)
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Апстракт
The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most impor...tant stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.

Извор:
New Journal of Chemistry, 2017, 41, 11, 4644-4661
Издавач:
  • Royal Soc Chemistry, Cambridge
Финансирање / пројекти:
  • Експериментална и теоријска проучавања реактивности и биолошка активност стереодефинисаних тиазолидина и синтетичких аналога (RS-172020)
Напомена:
  • This is the peer-reviewed version of the article: M. Baranac-Stojanovic, M. Stojanovic and J. Aleksic, New Journal of Chemistry, 2017, 41, 11, 4644-4661, https://dx.doi.org/10.1039/C7NJ00369B
  • http://cer.ihtm.bg.ac.rs/handle/123456789/2264

DOI: 10.1039/c7nj00369b

ISSN: 1144-0546

WoS: 000402377400045

Scopus: 2-s2.0-85021676909
[ Google Scholar ]
2
2
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2969
Колекције
  • Radovi istraživača / Researchers' publications
Институција/група
IHTM
TY  - JOUR
AU  - Baranac-Stojanović, Marija
AU  - Stojanović, Milovan
AU  - Aleksić, Jovana
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2969
AB  - The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.
PB  - Royal Soc Chemistry, Cambridge
T2  - New Journal of Chemistry
T1  - Theoretical study of azido gauche effect and its origin
VL  - 41
IS  - 11
SP  - 4644
EP  - 4661
DO  - 10.1039/c7nj00369b
ER  - 
@article{
author = "Baranac-Stojanović, Marija and Stojanović, Milovan and Aleksić, Jovana",
year = "2017",
abstract = "The strength of the azido gauche effect in 1,2-diazidoethane, N-(2-azidoethyl)ethanamide, (protonated) 2-azidoethanamine and (protonated) 2-azidoethanol and its origin were theoretically studied at the MP2/6-311++G(d,p) level of theory. The results show that the azido gauche effect in the amine and alcohol can exert a control over the molecular conformation to a similar extent as the fluorine gauche effect, but to a greater extent in the charged species, amide and vicinal diazido fragment. A quantitative partitioning of isomerization energy into contributions from electrostatic, orbital, dispersion and Pauli interactions and energy consumed in structural changes revealed that electrostatic forces play an important role in the stabilization of the gauche isomer in the two charged species and alcohol. Electrostatic and dispersion interactions are the main contributors to the gauche effect in the amide, whereas dispersion and orbital interactions can be considered to be the two most important stabilizing factors of the gauche form in the vicinal diazido fragment. The interplay of all three stabilizing interactions determines the gauche preference in the amine. Stereoelectronic effects, which are involved in orbital interactions, contribute to the gauche effect in all the molecules except the 2-azidoethylammonium ion and protonated 2-azidoethanol. Hydrogen-bonding interactions were found only in the protonated alcohol.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "New Journal of Chemistry",
title = "Theoretical study of azido gauche effect and its origin",
volume = "41",
number = "11",
pages = "4644-4661",
doi = "10.1039/c7nj00369b"
}
Baranac-Stojanović, M., Stojanović, M.,& Aleksić, J.. (2017). Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry
Royal Soc Chemistry, Cambridge., 41(11), 4644-4661.
https://doi.org/10.1039/c7nj00369b
Baranac-Stojanović M, Stojanović M, Aleksić J. Theoretical study of azido gauche effect and its origin. in New Journal of Chemistry. 2017;41(11):4644-4661.
doi:10.1039/c7nj00369b .
Baranac-Stojanović, Marija, Stojanović, Milovan, Aleksić, Jovana, "Theoretical study of azido gauche effect and its origin" in New Journal of Chemistry, 41, no. 11 (2017):4644-4661,
https://doi.org/10.1039/c7nj00369b . .

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